HCID 18727257, compound → HCID 18727204, compound

HRID 609694Notes

Reaction equation

HRID 609694 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[CH2:17][N:16]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:15][CH2:14][N:13]1[S:23]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[C:40]3[C:35](=[C:36]([F:44])[C:37]([F:43])=[C:38]([F:42])[C:39]=3[F:41])[NH:34][CH:33]=2)[CH2:28][CH2:27]1)(=[O:25])=[O:24])=[O:11])C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[OH:8][NH:9][C:10]([C@H:12]1[CH2:17][N:16]([C:18]([N:20]([CH3:21])[CH3:22])=[O:19])[CH2:15][CH2:14][N:13]1[S:23]([N:26]1[CH2:27][CH2:28][CH:29]([C:32]2[C:40]3[C:35](=[C:36]([F:44])[C:37]([F:43])=[C:38]([F:42])[C:39]=3[F:41])[NH:34][CH:33]=2)[CH2:30][CH2:31]1)(=[O:24])=[O:25])=[O:11]

Participants

4

Reactant 1

HCID 18727257HCID 18727257, compound

Product 1

HCID 18727204HCID 18727204, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of N-benzyloxy-4-(N,N-dimethylaminocarbonyl)-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (8.90 g, 13.97 mmol) [prepared as described in Step 6 above] in argon deoxygenated 80% ethanol/tetrahydrofuran (470 ml) was treated with 10% Pd/C (3.5 g) and stirred under a hydrogen atmosphere (1 atm) for 45 min. The reaction was degassed under argon, filtered through Celite, and the filtrate was concentrated in vacuo. Ethyl acetate (5 ml) was added and the solution was added dropwise to hexane (250 ml) with vigorous stirring. The solid was filtered to afford N-hydroxy-4-(N,N-dimethylaminocarbonyl)-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (96%) as a white solid.

Workup

  1. customThe reaction was degassed under argon
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionEthyl acetate (5 ml) was added
  5. additionthe solution was added dropwise to hexane (250 ml) with vigorous stirring
  6. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-f73323852e6a442d96fb580168fd0c6a
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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